Aniline → 4-(Heptafluoropropan-2-yl)aniline

HRID 2427293Notes

Reaction equation

HRID 2427293 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[C:9]([F:18])([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11].S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])O.[Na+]>COC(C)(C)C.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:18][C:9]([C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)([C:14]([F:17])([F:16])[F:15])[C:10]([F:13])([F:12])[F:11]

Participants

8

Reactant 4

HCID 6115AnilineHCID 24477Sodium ThiosulfateHCID 33978Perfluoroisopropyl iodideHCID 516892Sodium Bicarbonate

Product 1

HCID 98166664-(Heptafluoropropan-2-yl)anilineYield 27%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a solution of aniline (1.32 g, 14.19 mmol) in tert-butyl methyl ether (25 ml) and water (25 ml) was added sequentially 2-iodoheptafluoropropane (5.00 g, 17.06 mmol), sodium thiosulphate (3.50 g, 17.06 mmol), sodium hydrogen carbonate (1.73 g, 17.06 mmol) and tetrabutylammonium hydrogen sulphate (0.53 g, 17.06 mmol). The reaction mixture was stirred at room temperature for 18 h and the two layers were separated. The aqueous layer was extracted with ethyl acetate and the combined organic phases were washed with hydrochloric acid (2N), aqueous sodium hydrogen carbonate solution and brine, dried (MgSO4) and concentrated in vacuo to give the titled compound (1.00 g).

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic phases were washed with hydrochloric acid (2N), aqueous sodium hydrogen carbonate solution and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-48bbbd2d00c747fa9b322abbd590f775
Source dataset
uspto-grants-2011_06
Patent number
US07968584B2

Reaction notes

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